Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502636X/ob6564sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502636X/ob6564Isup2.hkl |
CCDC reference: 290313
Data collection: RAPID-AUTO (Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.
C16H27Cl3N2O5 | Dx = 1.264 Mg m−3 |
Mr = 433.75 | Melting point = 415–417 K |
Hexagonal, P65 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: P 65 | Cell parameters from 21563 reflections |
a = 12.1055 (14) Å | θ = 3.3–68.2° |
c = 26.939 (5) Å | µ = 3.85 mm−1 |
V = 3418.8 (8) Å3 | T = 173 K |
Z = 6 | Needle, colorless |
F(000) = 1368.00 | 0.30 × 0.01 × 0.01 mm |
? # Insert any comments here. |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.097 |
Detector resolution: 10.00 pixels mm-1 | θmax = 68.2° |
ω scans | h = −14→14 |
29240 measured reflections | k = −14→14 |
4134 independent reflections | l = −31→32 |
1326 reflections with F2 > 2σ(F2) |
Refinement on F2 | w = 1/[0.1σ(Fo2) + 2.0]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.043 | (Δ/σ)max < 0.001 |
wR(F2) = 0.079 | Δρmax = 1.14 e Å−3 |
S = 1.06 | Δρmin = −0.65 e Å−3 |
4134 reflections | Absolute structure: Flack (1983), 1992 Friedel pairs |
263 parameters | Absolute structure parameter: 0.05 (2) |
H-atom parameters constrained |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl41 | 0.70249 (14) | 0.13892 (18) | 0.55437 (6) | 0.0759 (5) | |
Cl42 | 0.78694 (16) | 0.3511 (2) | 0.62183 (6) | 0.0851 (6) | |
Cl43 | 0.53865 (16) | 0.12709 (19) | 0.63264 (6) | 0.0765 (5) | |
O101 | −0.2252 (4) | −0.1300 (3) | 0.61682 (12) | 0.0587 (10) | |
O102 | −0.1765 (5) | −0.0711 (3) | 0.53796 (13) | 0.0844 (14) | |
O201 | 0.1976 (3) | 0.1218 (3) | 0.59163 (12) | 0.0499 (11) | |
O301 | 0.4220 (3) | 0.3423 (4) | 0.53180 (16) | 0.0664 (13) | |
O401 | 0.4902 (3) | 0.2020 (4) | 0.53375 (12) | 0.0581 (11) | |
N201 | −0.0625 (3) | 0.0564 (4) | 0.59947 (12) | 0.0448 (12) | |
N301 | 0.1778 (3) | 0.1437 (4) | 0.51002 (14) | 0.0439 (12) | |
C101 | −0.3418 (6) | −0.2494 (5) | 0.6070 (2) | 0.0737 (19) | |
C102 | −0.3883 (7) | −0.3026 (7) | 0.6566 (2) | 0.098 (2) | |
C103 | −0.4377 (7) | −0.2222 (10) | 0.5836 (3) | 0.143 (3) | |
C104 | −0.3139 (13) | −0.3318 (8) | 0.5771 (4) | 0.162 (4) | |
C105 | −0.1566 (5) | −0.0495 (5) | 0.58122 (17) | 0.0464 (16) | |
C201 | 0.0292 (4) | 0.1567 (5) | 0.56708 (14) | 0.0380 (13) | |
C202 | 0.1402 (4) | 0.1392 (4) | 0.55772 (18) | 0.0362 (13) | |
C203 | 0.0738 (4) | 0.2865 (4) | 0.59201 (19) | 0.0393 (13) | |
C204 | 0.1523 (5) | 0.4006 (5) | 0.5584 (2) | 0.0568 (17) | |
C205 | 0.2060 (7) | 0.5224 (5) | 0.5901 (2) | 0.087 (2) | |
C206 | 0.0732 (6) | 0.4062 (6) | 0.5164 (2) | 0.070 (2) | |
C301 | 0.2858 (4) | 0.1316 (5) | 0.49924 (18) | 0.0468 (16) | |
C302 | 0.4038 (4) | 0.2403 (6) | 0.52338 (18) | 0.0470 (16) | |
C303 | 0.3090 (6) | 0.1349 (8) | 0.4433 (2) | 0.085 (2) | |
C401 | 0.6029 (5) | 0.2933 (6) | 0.5578 (2) | 0.066 (2) | |
C402 | 0.6567 (5) | 0.2319 (7) | 0.5900 (2) | 0.0630 (19) | |
H1 | −0.4028 | −0.2466 | 0.6767 | 0.100* | |
H2 | −0.4650 | −0.3823 | 0.6538 | 0.100* | |
H3 | −0.3240 | −0.3151 | 0.6713 | 0.100* | |
H4 | −0.4557 | −0.1679 | 0.6032 | 0.141* | |
H5 | −0.4026 | −0.1822 | 0.5527 | 0.141* | |
H6 | −0.5142 | −0.3006 | 0.5779 | 0.141* | |
H7 | −0.3923 | −0.4083 | 0.5714 | 0.180* | |
H8 | −0.2801 | −0.2902 | 0.5463 | 0.180* | |
H9 | −0.2552 | −0.3515 | 0.5924 | 0.180* | |
H10 | −0.0582 | 0.0700 | 0.6343 | 0.053* | |
H11 | −0.0122 | 0.1546 | 0.5368 | 0.048* | |
H12 | 0.0028 | 0.2917 | 0.6040 | 0.048* | |
H13 | 0.1259 | 0.2907 | 0.6191 | 0.048* | |
H14 | 0.2219 | 0.3948 | 0.5451 | 0.068* | |
H15 | 0.2561 | 0.5187 | 0.6165 | 0.099* | |
H16 | 0.2568 | 0.5955 | 0.5703 | 0.099* | |
H17 | 0.1359 | 0.5275 | 0.6034 | 0.099* | |
H18 | 0.0039 | 0.4121 | 0.5300 | 0.083* | |
H19 | 0.1223 | 0.4776 | 0.4955 | 0.083* | |
H20 | 0.0413 | 0.3299 | 0.4976 | 0.082* | |
H21 | 0.1368 | 0.1622 | 0.4839 | 0.056* | |
H22 | 0.2718 | 0.0525 | 0.5122 | 0.059* | |
H23 | 0.3817 | 0.1275 | 0.4358 | 0.111* | |
H24 | 0.2364 | 0.0691 | 0.4268 | 0.110* | |
H25 | 0.3231 | 0.2156 | 0.4324 | 0.111* | |
H26 | 0.6636 | 0.3410 | 0.5328 | 0.084* | |
H27 | 0.5857 | 0.3487 | 0.5770 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl41 | 0.0749 (11) | 0.1125 (13) | 0.0685 (9) | 0.0680 (10) | 0.0112 (8) | 0.0066 (8) |
Cl42 | 0.0596 (9) | 0.1154 (15) | 0.0830 (11) | 0.0457 (10) | −0.0121 (8) | −0.0095 (10) |
Cl43 | 0.0700 (10) | 0.1015 (12) | 0.0605 (8) | 0.0447 (9) | 0.0191 (7) | 0.0151 (8) |
O101 | 0.065 (2) | 0.046 (2) | 0.041 (2) | 0.0104 (18) | 0.0005 (18) | 0.0047 (17) |
O102 | 0.111 (3) | 0.064 (2) | 0.037 (2) | 0.012 (2) | 0.006 (2) | −0.0059 (19) |
O201 | 0.062 (2) | 0.068 (2) | 0.0360 (18) | 0.046 (2) | 0.0037 (17) | 0.0142 (17) |
O301 | 0.058 (2) | 0.059 (2) | 0.087 (3) | 0.033 (2) | 0.002 (2) | 0.009 (2) |
O401 | 0.045 (2) | 0.079 (2) | 0.065 (2) | 0.042 (2) | −0.0083 (17) | −0.008 (2) |
N201 | 0.046 (2) | 0.057 (2) | 0.029 (2) | 0.023 (2) | 0.0026 (19) | 0.0044 (19) |
N301 | 0.038 (2) | 0.068 (2) | 0.033 (2) | 0.032 (2) | −0.0010 (17) | 0.0028 (18) |
C101 | 0.067 (4) | 0.041 (3) | 0.078 (4) | 0.000 (3) | 0.011 (3) | 0.003 (3) |
C102 | 0.083 (5) | 0.066 (4) | 0.100 (5) | 0.005 (3) | 0.013 (4) | 0.021 (4) |
C103 | 0.041 (4) | 0.132 (8) | 0.180 (10) | −0.012 (4) | −0.030 (5) | 0.025 (7) |
C104 | 0.166 (11) | 0.055 (4) | 0.229 (11) | 0.028 (5) | 0.062 (8) | −0.022 (6) |
C105 | 0.047 (3) | 0.048 (3) | 0.031 (3) | 0.014 (2) | 0.016 (2) | 0.007 (2) |
C201 | 0.039 (2) | 0.057 (3) | 0.024 (2) | 0.028 (2) | −0.0022 (19) | 0.005 (2) |
C202 | 0.045 (2) | 0.040 (2) | 0.030 (2) | 0.026 (2) | 0.003 (2) | 0.007 (2) |
C203 | 0.036 (2) | 0.040 (2) | 0.044 (2) | 0.021 (2) | 0.007 (2) | 0.004 (2) |
C204 | 0.060 (3) | 0.051 (3) | 0.059 (3) | 0.028 (2) | 0.010 (2) | 0.021 (2) |
C205 | 0.104 (5) | 0.047 (3) | 0.097 (5) | 0.028 (3) | 0.035 (4) | 0.017 (3) |
C206 | 0.066 (3) | 0.066 (3) | 0.074 (4) | 0.030 (3) | −0.003 (3) | 0.015 (3) |
C301 | 0.030 (2) | 0.081 (4) | 0.037 (2) | 0.033 (2) | −0.001 (2) | 0.003 (2) |
C302 | 0.043 (3) | 0.069 (3) | 0.038 (2) | 0.035 (2) | 0.010 (2) | 0.011 (2) |
C303 | 0.070 (4) | 0.151 (7) | 0.056 (3) | 0.071 (5) | 0.006 (3) | −0.010 (3) |
C401 | 0.045 (3) | 0.092 (4) | 0.074 (4) | 0.043 (3) | −0.009 (3) | 0.001 (3) |
C402 | 0.062 (3) | 0.088 (4) | 0.050 (3) | 0.045 (3) | −0.001 (3) | 0.006 (3) |
Cl41—C402 | 1.766 (9) | N301—H21 | 0.950 |
Cl42—C402 | 1.740 (5) | C102—H1 | 0.950 |
Cl43—C402 | 1.777 (5) | C102—H2 | 0.950 |
O101—C101 | 1.453 (6) | C102—H3 | 0.950 |
O101—C105 | 1.323 (5) | C103—H4 | 0.950 |
O102—C105 | 1.192 (5) | C103—H5 | 0.950 |
O201—C202 | 1.228 (7) | C103—H6 | 0.950 |
O301—C302 | 1.163 (9) | C104—H7 | 0.950 |
O401—C302 | 1.368 (9) | C104—H8 | 0.950 |
O401—C401 | 1.412 (6) | C104—H9 | 0.950 |
N201—C105 | 1.312 (5) | C201—H11 | 0.950 |
N201—C201 | 1.456 (5) | C203—H12 | 0.950 |
N301—C202 | 1.355 (6) | C203—H13 | 0.950 |
N301—C301 | 1.418 (8) | C204—H14 | 0.950 |
C101—C102 | 1.467 (9) | C205—H15 | 0.950 |
C101—C103 | 1.495 (14) | C205—H16 | 0.950 |
C101—C104 | 1.448 (16) | C205—H17 | 0.950 |
C201—C202 | 1.482 (9) | C206—H18 | 0.950 |
C201—C203 | 1.537 (7) | C206—H19 | 0.950 |
C203—C204 | 1.523 (6) | C206—H20 | 0.950 |
C204—C205 | 1.538 (8) | C301—H22 | 0.950 |
C204—C206 | 1.505 (9) | C303—H23 | 0.950 |
C301—C302 | 1.522 (6) | C303—H24 | 0.950 |
C301—C303 | 1.530 (7) | C303—H25 | 0.950 |
C401—C402 | 1.488 (12) | C401—H26 | 0.950 |
N201—H10 | 0.950 | C401—H27 | 0.950 |
C101—O101—C105 | 122.7 (4) | C101—C103—H6 | 108.9 |
C302—O401—C401 | 115.6 (5) | H4—C103—H5 | 109.5 |
C105—N201—C201 | 121.2 (3) | H4—C103—H6 | 109.5 |
C202—N301—C301 | 119.9 (4) | H5—C103—H6 | 109.4 |
O101—C101—C102 | 103.8 (4) | C101—C104—H7 | 107.3 |
O101—C101—C103 | 109.4 (6) | C101—C104—H8 | 107.9 |
O101—C101—C104 | 110.0 (7) | C101—C104—H9 | 113.1 |
C102—C101—C103 | 108.1 (7) | H7—C104—H8 | 109.5 |
C102—C101—C104 | 112.0 (7) | H7—C104—H9 | 109.5 |
C103—C101—C104 | 113.0 (8) | H8—C104—H9 | 109.5 |
O101—C105—O102 | 124.3 (4) | N201—C201—H11 | 108.6 |
O101—C105—N201 | 111.5 (3) | C202—C201—H11 | 110.7 |
O102—C105—N201 | 124.2 (4) | C203—C201—H11 | 108.3 |
N201—C201—C202 | 110.5 (5) | C201—C203—H12 | 110.5 |
N201—C201—C203 | 108.8 (3) | C201—C203—H13 | 106.0 |
C202—C201—C203 | 109.9 (3) | C204—C203—H12 | 108.5 |
O201—C202—N301 | 120.3 (5) | C204—C203—H13 | 108.2 |
O201—C202—C201 | 121.9 (4) | H12—C203—H13 | 109.5 |
N301—C202—C201 | 117.7 (4) | C203—C204—H14 | 109.3 |
C201—C203—C204 | 114.1 (4) | C205—C204—H14 | 108.4 |
C203—C204—C205 | 108.2 (4) | C206—C204—H14 | 109.1 |
C203—C204—C206 | 111.4 (4) | C204—C205—H15 | 110.1 |
C205—C204—C206 | 110.4 (6) | C204—C205—H16 | 110.3 |
N301—C301—C302 | 109.8 (5) | C204—C205—H17 | 107.9 |
N301—C301—C303 | 111.4 (5) | H15—C205—H16 | 109.5 |
C302—C301—C303 | 108.5 (4) | H15—C205—H17 | 109.5 |
O301—C302—O401 | 123.3 (4) | H16—C205—H17 | 109.5 |
O301—C302—C301 | 126.8 (6) | C204—C206—H18 | 108.7 |
O401—C302—C301 | 109.9 (6) | C204—C206—H19 | 111.2 |
O401—C401—C402 | 111.7 (5) | C204—C206—H20 | 108.5 |
Cl41—C402—Cl42 | 110.7 (4) | H18—C206—H19 | 109.5 |
Cl41—C402—Cl43 | 107.0 (4) | H18—C206—H20 | 109.5 |
Cl41—C402—C401 | 110.9 (4) | H19—C206—H20 | 109.5 |
Cl42—C402—Cl43 | 110.2 (3) | N301—C301—H22 | 108.7 |
Cl42—C402—C401 | 108.4 (5) | C302—C301—H22 | 109.4 |
Cl43—C402—C401 | 109.7 (4) | C303—C301—H22 | 109.0 |
C105—N201—H10 | 119.0 | C301—C303—H23 | 111.9 |
C201—N201—H10 | 119.6 | C301—C303—H24 | 110.9 |
C202—N301—H21 | 120.5 | C301—C303—H25 | 105.5 |
C301—N301—H21 | 119.4 | H23—C303—H24 | 109.5 |
C101—C102—H1 | 111.9 | H23—C303—H25 | 109.5 |
C101—C102—H2 | 109.9 | H24—C303—H25 | 109.5 |
C101—C102—H3 | 106.6 | O401—C401—H26 | 107.6 |
H1—C102—H2 | 109.5 | O401—C401—H27 | 109.6 |
H1—C102—H3 | 109.5 | C402—C401—H26 | 108.5 |
H2—C102—H3 | 109.5 | C402—C401—H27 | 109.8 |
C101—C103—H4 | 113.0 | H26—C401—H27 | 109.5 |
C101—C103—H5 | 106.4 | ||
C101—O101—C105—O102 | −6.9 (12) | N201—C201—C202—O201 | −49.8 (5) |
C101—O101—C105—N201 | 174.3 (6) | N201—C201—C202—N301 | 130.6 (4) |
C105—O101—C101—C102 | −176.9 (7) | N201—C201—C203—C204 | −170.0 (5) |
C105—O101—C101—C103 | −61.6 (9) | C202—C201—C203—C204 | 68.9 (6) |
C105—O101—C101—C104 | 63.1 (10) | C203—C201—C202—O201 | 70.3 (5) |
C302—O401—C401—C402 | 150.4 (5) | C203—C201—C202—N301 | −109.3 (4) |
C401—O401—C302—O301 | 2.8 (7) | C201—C203—C204—C205 | −171.9 (6) |
C401—O401—C302—C301 | −178.1 (4) | C201—C203—C204—C206 | 66.5 (7) |
C105—N201—C201—C202 | −91.6 (6) | N301—C301—C302—O301 | −29.1 (7) |
C105—N201—C201—C203 | 147.7 (6) | N301—C301—C302—O401 | 151.8 (4) |
C201—N201—C105—O101 | 177.2 (6) | C303—C301—C302—O301 | 92.9 (8) |
C201—N201—C105—O102 | −1.6 (11) | C303—C301—C302—O401 | −86.2 (6) |
C202—N301—C301—C302 | −61.6 (6) | O401—C401—C402—Cl41 | 63.2 (5) |
C202—N301—C301—C303 | 178.2 (4) | O401—C401—C402—Cl42 | −175.1 (4) |
C301—N301—C202—O201 | −1.6 (6) | O401—C401—C402—Cl43 | −54.8 (6) |
C301—N301—C202—C201 | 178.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N201—H10···O102i | 0.95 | 1.97 | 2.907 (5) | 171 |
N301—H21···O201ii | 0.95 | 1.89 | 2.829 (6) | 170 |
Symmetry codes: (i) y, −x+y, z+1/6; (ii) x−y, x, z−1/6. |